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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:32:19 UTC
Update Date2020-11-09 23:29:35 UTC
HMDB IDHMDB0029737
Secondary Accession Numbers
  • HMDB29737
Metabolite Identification
Common NameIndole-3-carboxaldehyde
DescriptionIndole-3-carboxaldehyde (I3A), also known as 3-formylindole or 3-indolealdehyde, belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. I3A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, I3A has been detected, but not quantified in, several different foods, such as gram beans, Brussels sprouts, cucumbers, cereals and cereal products, and white cabbages. This could make I3A a potential biomarker for the consumption of these foods. I3A is found in barley, tomato seedlings, and cotton. I3A has also been found to be a microbial metabolite of Clostridium and Lactobacillus (PMID: 30120222 , 27102537 ).
Structure
Data?1586965572
Synonyms
ValueSource
Indole-3-carbaldehydeKEGG
1H-Indole-3-carbaldehydeHMDB
1H-Indole-3-carboxaldehdeHMDB
3-FormylindoleHMDB, ChEBI
3-IndolealdehydeHMDB, ChEBI
3-IndolecarbaldehydeHMDB, ChEBI
3-IndolecarboxaldehydeHMDB, ChEBI
3-IndolemethanalHMDB, MeSH
b-IndolylaldehydeHMDB, Generator
beta-IndolylaldehydeHMDB, ChEBI
indol-3-CarbaldehydHMDB
indol-3-CarbaldehydeHMDB
indol-3-CarboxaldehydeHMDB
Indole-3-aldehydeHMDB, ChEBI
INDOLE-3-carboxyaldehydeHMDB
1H-Indole-3-carboxaldehydeChEBI
I3choChEBI
Indole-3-carboxaldehydeChEBI
β-IndolylaldehydeGenerator
1H-Indol-3-yl carboxaldehydeHMDB
1H-Indole-3-aldehydeHMDB
1H-Indole-3-methanalHMDB
3-Formyl-1H-indoleHMDB
3-IndolylformaldehydeHMDB
I3AHMDB
Indole-3-carboxylaldehydeHMDB
Indole-3-formaldehydeHMDB
Chemical FormulaC9H7NO
Average Molecular Weight145.158
Monoisotopic Molecular Weight145.052763851
IUPAC Name1H-indole-3-carbaldehyde
Traditional Nameindole-3-carboxaldehyde
CAS Registry Number487-89-8
SMILES
O=CC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H
InChI KeyOLNJUISKUQQNIM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • Indole
  • Aryl-aldehyde
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point197 - 199 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.68Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.46 g/LALOGPS
logP1.92ALOGPS
logP1.78ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)13.54ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.86 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.73 m³·mol⁻¹ChemAxon
Polarizability15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kp-7900000000-cfb69fae32949705791fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-2900000000-90cfb2317bcbb908e2e8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-2900000000-90cfb2317bcbb908e2e8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-2900000000-c43b940db5ef735c79d6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kk-2950000000-8901bc9a710fac996fbcSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-2960000000-0b154d6ce8924292e9edSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-252f37d7921252e01ac0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-868873ec5dc494bef752Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kp-7900000000-cfb69fae32949705791fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-2900000000-90cfb2317bcbb908e2e8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-2900000000-90cfb2317bcbb908e2e8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-2900000000-c43b940db5ef735c79d6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kk-2950000000-8901bc9a710fac996fbcSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-2960000000-0b154d6ce8924292e9edSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-252f37d7921252e01ac0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-868873ec5dc494bef752Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-0900000000-2f4c23a8137235ce4e95Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0900000000-39d11dbd7bebe565fa94Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014l-0900000000-c9a64e9031a8d467a02bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0900000000-b7ccb1c640ee7aaf06b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014l-0900000000-d434c2e937c83d1ffd7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kb-0900000000-597c804d77e9a7930c9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-2900000000-878ab4a0cfc6d8f0e9d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kf-9400000000-74dbc81ab5e686655977Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kf-9100000000-22b52274e9bec85c9488Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-3900000000-b8cbcf3139ea5a313666Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-2900000000-94ec8ba0db56440ffc3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-68769392454e8a8bc1daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-0be256e552c87fb9650aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2900000000-ae05266446e712d329cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-89f321c95d799e3073a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-f63834b99989e7eab9cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-2900000000-7f76bc218a02b8adc1d0Spectrum
MSMass Spectrum (Electron Ionization)splash10-0007-2900000000-fcb37c6394c016a4e2d0Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000934
KNApSAcK IDC00000112
Chemspider ID9838
KEGG Compound IDC08493
BioCyc IDINDOLE-3-CARBOXALDEHYDE
BiGG IDNot Available
Wikipedia LinkIndole-3-carboxaldehyde
METLIN IDNot Available
PubChem Compound10256
PDB IDI3A
ChEBI ID28238
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Roager HM, Licht TR: Microbial tryptophan catabolites in health and disease. Nat Commun. 2018 Aug 17;9(1):3294. doi: 10.1038/s41467-018-05470-4. [PubMed:30120222 ]
  2. Zhang LS, Davies SS: Microbial metabolism of dietary components to bioactive metabolites: opportunities for new therapeutic interventions. Genome Med. 2016 Apr 21;8(1):46. doi: 10.1186/s13073-016-0296-x. [PubMed:27102537 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .